(1-docosanyl) 2,3-anhydro-6-deoxy-α-L-rhamno-pyranoside | 1234623-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-docosanyl) 2,3-anhydro-6-deoxy-α-L-rhamno-pyranoside
• 英文别名: (1R,2R,4S,5S,6R)-2-docosoxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 1234623-78-9
• 化学式: C₂₈H₅₄O₄
• 分子量: 454.734
• InChiKey: MZBGKJKNTBKRBX-UZSVIBPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-docosanyl) 2,3-anhydro-6-deoxy-α-L-rhamno-pyranoside 、 乙酸酐 在 lithium aluminium tetrahydride 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 96.0h， 以80%的产率得到(1-docosanyl) 2,4-di-O-acetyl-3,6-dideoxy-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis and Raman spectra of 3-deoxy-α-l-rhamnosides as model sugars of the Ascaris egg shell

  摘要：

  The synthesis of two 3-deoxy-alpha-L-rhamnosides (i.e., 3,6-dideoxy-L-arabino-hexopyranosides) as models of ascaroside natural products is reported. The present approach is based on a Ferrier rearrangement from L-rhamnal, epoxidation of the resulting glycal and reductive opening of the isolated beta-epoxide. The 3-deoxy-alpha-rhamnoside linked to a long aglycone chain was used to ascertain by Raman vibrational spectroscopy the presence of this peculiar sugar in the inner shell of Ascaris eggs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.061
• 作为产物：
  描述：

  (1'-docosanyl) 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯甲腈 为溶剂， 反应 48.0h， 以14%的产率得到(1-docosanyl) 2,3-anhydro-6-deoxy-α-L-allo-pyranoside
  参考文献：
  名称：

  Synthesis and Raman spectra of 3-deoxy-α-l-rhamnosides as model sugars of the Ascaris egg shell

  摘要：

  The synthesis of two 3-deoxy-alpha-L-rhamnosides (i.e., 3,6-dideoxy-L-arabino-hexopyranosides) as models of ascaroside natural products is reported. The present approach is based on a Ferrier rearrangement from L-rhamnal, epoxidation of the resulting glycal and reductive opening of the isolated beta-epoxide. The 3-deoxy-alpha-rhamnoside linked to a long aglycone chain was used to ascertain by Raman vibrational spectroscopy the presence of this peculiar sugar in the inner shell of Ascaris eggs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.061

文献信息

• Synthesis and Raman spectra of 3-deoxy-α-l-rhamnosides as model sugars of the Ascaris egg shell
  作者：Jean-Pierre Joly、Frédéric Roze、Sandrine Banas、Fabienne Quilès

  DOI：10.1016/j.tetlet.2010.04.061

  日期：2010.6

  The synthesis of two 3-deoxy-alpha-L-rhamnosides (i.e., 3,6-dideoxy-L-arabino-hexopyranosides) as models of ascaroside natural products is reported. The present approach is based on a Ferrier rearrangement from L-rhamnal, epoxidation of the resulting glycal and reductive opening of the isolated beta-epoxide. The 3-deoxy-alpha-rhamnoside linked to a long aglycone chain was used to ascertain by Raman vibrational spectroscopy the presence of this peculiar sugar in the inner shell of Ascaris eggs. (C) 2010 Elsevier Ltd. All rights reserved.